Water → HCID 67401333, compound

Participants

Reaction Steps

Sixty percent sodium hydride (in oil) (224 mg, 5.6 mmol) was suspended in tetrahydrofuran (5 mL). To this, triethyl 2-phosphonopropionate (1.2 mL, 5.6 mmol) was added under a nitrogen atmosphere with cooling in an ice bath and the mixture was stirred at the same temperature for 30 minutes. To this, 3-pyridinecarboxaldehyde (300 mg, 2.8 mmol) was added and the mixture was stirred at the same temperature for 1.5 hours. After water was added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 2/1) to give ethyl 2-methyl-3-(pyridin-3-yl)acrylate (480 mg, yield: 90%).

Provenance & Evidence